DEO Profile: Emily Pilloton

Executive Director of Project H Design Director of Creativity at REALM Charter School

Maria Giudice & Christopher Ireland
Rise of the DEO
11 min readJul 3, 2019

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On one arm Emily Pilloton wears colorful string bracelets woven by her students. On the other she wears a sleekly designed smart watch. Like all DEOs, she is a study in contrasts. A self-admitted nerd who loves math and art. A teacher who loves structure and chaos. A woman who is empathetic and fierce.

We met Pilloton on a warm evening in an Oakland neighborhood café. Although tired from weeks of running her newest venture, Studio G, she took time to share the story of her young but impressive career.

Can you recall any early childhood experiences that shaped you?

I grew up in a house in the woods and spent most of my days building tree houses, naming rocks, and building forts. My two younger sisters were my first creative collaborators in a way. Because our house was in the middle of nowhere, we had to make our own fun. I have beautiful memories of growing up in that house and being able to play and learn in really organic, unintentional ways. I imagine a lot of my design sensibilities and my love of architecture and place came from that.

I also grew up in the age of MacGyver and seeing his problem solving. I had a huge crush on him. I mean, I think you could argue that he was the original design thinker.

When did you first believe you could lead?

My sense of leadership really came more through others’ validation rather than my own awareness. In elementary and middle school, I was a black sheep in a lot of ways. I was a big nerd and the only nonwhite kid in the class for a long time. I felt out of place except when I played tennis. In my junior year of high school, my team had to select a captain. I didn’t really think that was something I wanted to do, but then everyone silently voted for me to be the team captain.

So I was like, oh, well, maybe people don’t think I’m such a weirdo. Others saw potential in me that I hadn’t seen in myself.

Why did you start your first company?

I had close to $100,000 in loans to pay off after graduate school. I went the traditional path and got a job designing furniture and working for an architecture firm just to pay my bills. That didn’t last very long. I realized quickly that I don’t do well working for other people. I have some problems with authority. I really just want to do my own thing.

I was disenchanted with the idea of working for seven different bosses, and with doing projects that didn’t have my own heart and soul in them — like choosing doorknobs and other such ridiculous things. It didn’t feel very important and it felt disconnected from who I was, the things I believed in, and the power I knew design could have in the world.

So I left the real world of having a job and a 401(k) and started a nonprofit. I didn’t know any other way than to just try to figure it out, so I wrote the articles of incorporation for a non-profit called Project H. The mission statement originally was rooted in four H words: humanity, habitat, health, and happiness. I had this inkling that there were other young designers who probably felt the same way.

Emily travels from her tree house to a career in transformations.

Did you face any barriers in starting Project H?

Sure, like suddenly you have to raise money. I spent the first six months sending cold-call emails to people I admired or people I wanted to work with — people like Cameron Sinclair and Architecture for Humanity. He let me work in their space and people would come in and out of there, and I would talk to them. When anyone I came across seemed even remotely interested, I would email them. Maybe 30 percent of them responded.

The only way I knew to start was just to start having conversations, and then things started to stick. It was one of those things where I felt like if I led with confidence (even if I was faking it), at least I’d be in the right scenarios to figure it out. I discovered within the first month that I wasn’t alone. There were people I’d gone to grad school with or people here in the Bay Area at CCA (California College of the Arts) or the Academy of Art or UC Berkeley who were feeling the same kind of disenchantment with the design industry as we know it. Finding this sense of community helped. Even though I didn’t know what projects might come of it, I knew there were others like me.

I still don’t know what I’m doing all the time right now, but I have that first year to thank for building a sense of community and projects that turned into even bigger projects that have sustained us for a long time.

When did you start teaching creativity?

At the very beginning, we started working with groups around the world on a really local level, just trying to inject a creative process to produce solutions that were meaningful to people. I wrote the book Design Revolution and toured the country in an Airstream trailer that we turned into an exhibition space.

We let people engage and play with the designs, and we added some lectures and workshops around the power of design. We went everywhere, from the best design schools to random elementary schools in the middle of Louisiana.
It was a great way to learn what this kind of work means in the bigger sphere, beyond the design community and my own little organization.

In the spring of 2009, I got this random email from a superintendent named Dr. Chip Zullinger, who was the superintendent of a school district in northeastern North Carolina called Bertie County. The whole northeastern part of the state is really rural and really poor, and this district in particular was struggling. Dr. Z reached out to us after seeing the Learning Landscape, an educational playground we designed that could be built in a day for free.

Over the course of two weeks, my partner and I got the email, booked flights, and flew to this place that’s in the middle of nowhere. We built four playgrounds in four days. We then did six or seven more projects with him. After nine or ten months of traveling back and forth we pitched the idea of us becoming high school teachers. We figured that if we really wanted to be serious about design in public education, we needed to be in the classroom.

Were you confident this would work?

We were totally naive about what that involved. We pitched the idea that we’d bring back vocational education, but with a twist. We’d teach the hard skills — construction, masonry, carpentry, welding, digital fabrication, graphic design — all these things that were really relevant within industries, but then we’d infuse them with two things new to vocational education: design and a focus on community. We’d ask our students to design something the community needed and then build it.

But while creativity is natural to me, it became very clear that it was not natural to the students. I’d have these fifteen-, sixteen-, seventeen-year-olds who had gone through years of education that drained the creativity out of them. We may as well have been teaching them Arabic or something. It’s so completely outside of their mode of operation.

They looked at me like I was crazy, but the minute they started to see their ideas come to life at full-scale, that was the moment where I think they realized this isn’t just about models on a desk. As a group, I think that was the biggest moment for them.

What would you say was your biggest mistake and what did you learn from it?

The whole discourse around failure and mistakes I think is almost a misnomer. It’s important to fail because you’ll learn from it, but in my mind, that’s not really a failure. All you’re doing is acting and making a decision and responding to it. Sometimes a decision has negative consequences. Sometimes there are positive consequences. But I almost don’t even view them as mistakes or failures. They are things that happened that I had to respond to.

There are certainly projects that we’ve done that haven’t turned out well. When we first got started as a nonprofit, we worked with this group in South Africa on a water transport device called the Hippo Roller. We partnered with an organization to redesign it. But we didn’t have a lot of foresight about how tough it would be to manage a project that was so product centric and a world away, where you’re not really connected to the place. That project was a failure, but in the best way because it helped us find our way and take on other projects.

Has your leadership style evolved?

I don’t often think of my leadership skills or lack of skills in a focused way, but teaching has influenced how I lead. I’m definitely a control freak in some ways, but having to stand in front of a class of young people every day and be both compassionate and a disciplinarian moderates that. I think I’ve gotten a lot better at dancing the line between the hug and the smack upside the head, and that’s a constant balance. I think kindness always rules, but every now and then you have to put your foot down. Being a woman, my nature is to be compassionate, but there are times when I’m like, okay, get your shit together.

My latest venture, Studio G, is the first time I’ve had to curate a team, not just work with one other partner. I needed to hire seven people who were all different, amazing, and worked well together. I had to give up a lot of what I wanted, but I got things from my team that I couldn’t get otherwise.

How do you lead in a time of so much change?

The whole idea of leadership is kind of secondary to me — it’s never really been my goal. The part of design that I really like is the intimacy of it. I like being in spaces where the design process can be really intimate, where you know the details of your student’s family, and you can work with them on something that they want to create.

Education is a really tumultuous space, and it can feel really overwhelming, but when you’re sitting next to a twelve-year-old who wants to build a floating island in the middle of the ocean, there’s something really sweet and simple about it too.

I try to seek out those opportunities that feel really intimate, but that are part of something that’s a lot bigger.

Maybe that’s what makes me a good leader — having those one-on-one experiences. I don’t ever want to be in a position where I don’t have that.

What do you love about your current job?

I love the intense intimacy of the work. When I was working in North Carolina, I would go home crying and come to school the next day totally rejuvenated. Now the context is different, but the feeling and the heart of it is very similar. It’s obviously a more complex urban environment. There’s just more of everything: more kids, more social workers, more drugs, more baggage that kids come to school with. But it all boils down to those small moments and that’s what I try to focus on.

What’s your superpower or key strength and what’s your Kryptonite?

My Kryptonite for sure is that I’m impatient. If I start something, I’m damn well going to finish it. If my progress is held up, it drives me berserk. I’m also learning to delegate. Just yesterday I was thinking, “Why should I walk someone through my accounting system when I could do it myself in two hours while drinking coffee?” Then I realize that I need to grow up and have a real bookkeeping system.

As for my strength, I think I’m pretty good at keeping people motivated across a range of abilities. In my current program we have everything from high-performing students to ones who come twice a week if we’re lucky. I can inspire both ends of that spectrum. I’m a good listener with students and other people.

Teaching a young girl how to handle power tools.

Do you have a company culture?

My motto was always “designing with people instead of for people.” Now I’d say it’s “designing with and for and by people.” It’s not just about me and my design, but about how can I support others so they can design for themselves.

Also, I emphasize systems, not stuff. There’s design porn everywhere — sleek, shiny things. To me that just feels like you’re missing the whole story of where the design came from and the people who are going to use it. I’m more interested in design that’s sometimes invisible, that isn’t a product, but rather this wonderful process that someone’s really thought through that makes people’s lives easier and more beautiful or more loving. I think design is so synonymous with the “thing,” like the iPad, that it’s hard to separate the two.

Do you think innovation depends more on process or people?

Our process is that there is no process. We defer to our students because we want them to have their own processes. But our approach is still rigorous. No matter what we’re doing, you’re going do it a hundred times. You’re going to be better for it, for having done it ninety-nine more times than you wanted to. That’s a tough sell to a seventeen-year-old, but I really love it when you’re getting somewhere just by doing the work.

I’ve never really had a plan for our company. People will ask me what my five-year plan is and I tell them to ask me in four years. That sounds horrible, but I think especially in my own career, I want the flexibility to discover what’s out there and be able to do that and not have a board of trustees that stops me because it’s not in my strategic plan. Everything we’ve done that’s special or successful or extraordinary has been a happy accident. Our design process embraces spontaneity and I want to be able to do that with my organization.

What three things do you want to be known for?

If someone describes me as all heart, I’ll feel like that was the best thing ever. Also that I was fearless and that I was awed. I mean I think that’s kind of an asset as a leader — acknowledging that it’s all a work in progress. The design work, the life work, isn’t that what design is — just trying to make everything better every step of the way? I think that’s true for my life, too. I keep making mistakes and then trying to correct them, and then I’ll make another one. I think that’s what makes it really fun.

To go to the first DEO profile go here. To start at the beginning, go here.

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